Azo dye.



UNITED STATES PATENT OFFICE.

LEOPOLD HESSE AND OSCAR Gij'NTI-IER, OF ELBERFELD, AND ARTHUR ZAR'I, OF VOI-I- WINKEL, NEAR ELBERFELD, GERMANY, ASSIGNORS TO FARBENFABRIKEN VORM. FRIEDR. BAYER & (30., OF ELBERFELD, GERMANY, A CORPORATION OF GERMANY.

AZO DYE.

Specification of Letters Patent. Patented Sept. '7, 1909.

933,446. No Drawing. Application filed April 8, 1909. Serial No. 488,696.

T all whom it may concern: chloric acid the dyestuffs are decomposed, an 55 Be it known that we, LEOPOLD HESSE, Osortho-substituted amin, a diamin' and a (le- CAR GiiN'rHER, and ARTHUR ZART, doctors rivative of a 2.6-diamino--naphthol comof philosophy, chemists, citizens of the Gerpound having the formula: 5 man Empire, residing at, respectively, BL X berfeld, Elberfeld, and Vohwinkel, near Eli 60 berfeld, Kingdom of Prussia, Germany, have invented new and useful Improvements in Azo ColoringfiMatter, of which the folowin is a spec1 cation.

Oui present invention relates to the manu- G 5 facture and production of new secondary 0H disazo dyestuffs dyeing cotton from red to are f d blue shades which are remarkable for their I Order to can-y out i Process we can extl'aoldmary fastness to light. 0. g. proceed as follows, the parts being by The F y are obtame y p fl weight: 173.5 parts of anilin-ortho-sultonic s amlnoazo p fronl {hazotlzed acid are diazotized with 69 parts of sodium amins of the benzene seriescontaining a negi it d th necessary ti f h d atlve 'Q P ortho pq to h 9 1 chloric acid and the dia-zo compound thus groullwlfl1 suktable alums: then t i g produced is then combined with 187.5 parts these lntelmedlate Products and comblmflg of cresidin hydrochlorid in the usual way the thus produced diazoazo compounds with ith th dditi f di t t 1 d 2-am1no-5-naphthol compounds having the hl id i dd d d th azo d i filformula: tered off, the intermediate compound after 25 x transformation into the sodium salt, is res03H dissolved in water and is then rediazotized at 1520 (l, the diazo compound is salted outhand filtered 013?. It is then stirred up wit water to a aste an is added to an 30 alkaline solution f 322 parts of 5-oXy-1.2-

on phenylfrfiaphthimidazol-7-sulfonic acid. The 5 yestu is then isolated in the usual way.

( X i i ii i l such as It is after being dried and pulverized in the or Z or X shape of its sodluin salt a dark powder 35 R1 soluble in water with a reddish-violet color l Rand R=H and soluble in concentrated sulfuric acid y or alkyl with a blue color. By reduction with stane. g. the thiazol deprivaties of the Q-amino- P0115 chlol'ld a11d hydrochlorlc 9 h y 5 naphthol 7 lf i id (See United is decomposed anilin-ortho-sulfonic acid, 2.5-

40 States Letters Patent 795869) or the imid1am1n'4'mth OXytO1uene a y' dazol derivaties of 2amino-5-naphth0l-7- phenylnaphthlmldazol'eammo 7 Sulfonlc sulfonic acid (see United States Letters Patfield are formed- It y cotton fast blue ent 792600), the carbonyl-1.2-diamino-5- Shadesnaphthol-7-sulfonic acid. The process 1s carrled out in an analogous 45 T Produce th aminoazo compounds from manner on starting from other amins condiazo compounds whi h ombine o ly ith t aining a negative group in ortho-position difliculty one can make use of the process det0 th amin -group such as para-toluidinscribed in British Letters Patent 11343 of ortho-sulfonic acid, meta-xylidin-ortho-sul- 1899. fonic acid, para-chloroanilin-ortho-sulfonic 50 The new dyest-ufl's are in the shape of their acid, para nitranilin ortho sulfonic acid,

alkaline salts dark powders easily soluble in anilin-QA-disulfonic acid, ortho nitranilinwater, soluble in concentrated sulfuric acid para-sulfonic acid, or on using other middle wit-h from a violet to green color. Upon recomponents to form the aminoazo comduction with stannous chlorid and hydropounds, such as anilin, cresidin, alpha-naphthylamin, alpha-naphthylamin-6- or 7-sulfonic acid or on using carbonyl-1.2-diamino- 5-naphtl1ol 7 sulfonic acid, meta aminophenyl 1.2 naphthothiazol-5-oxy-7-sulfonic acid, etc. as end components.

We claim:

1. The herein described new azo dyestufi's obtainable from aminoazo compounds which contain in the first component which is a benzene derivative a negative group in ortho-position to the amino-group with the hereiubefore defined 2 amino 5 naphthol compounds, which dyestufi's are, after being dried and pulverized, in the shape of their alkaline salts dark powders soluble in Water, soluble in concentrated sulfuric acid with from a violet to green color; yieldin upon reduction with stannous chlorid an hydrochloric acid an ortho-substit-uted amin of the benzene series, a diamin and a derivative of a 2.6-diamino-5-naphthol compound of the above given formula; and dyein cotton from red to blue shades, substantia 1y as described.

[SEAL-1 Corrections in Letters Patent No. 933,446.

2. The herein described new azo dyestuif which can be obtained from anilin-ortho-sul' fonic acid, cresidin and 5-oxy-L2-phenyluaphthimidaZ0l-7-sulf0nic acid, which dyestufi' is, after being dried and pulverized, in the shape of its sodium salt a dark powder which is soluble in water with a reddishviolet color and which is soluble in concentrated sulfuric acid with a blue color; yielding upon reduction with stannous chlorid and hydrochloric acid anilin-ortho-sulfonic acid, 2.5-dia1nino-4-1nethoxytoluene and 5- oxy-1.2-phenynaphthimidazol-G-amino-T-sulfonic acid; and dyeing cotton blue shades, substantially as described.

In testimony whereof We have hereunto set our hands in the presence of two subscribing witnesses.

Witnesses O'r'ro KoNIG, C. J. WRIGHT.

It is hereby certified that in Letters Patent No. 933,4:46, granted September 7 1909, upon the application of Leopold Hesse and Oscar Gunther, of Elberfeld, and

Arthur Zart, of Vohwi'nkel, near Elberfeld, Germany, for an improvement in Azo Dyes, errors appear in the printed specification requiring correction as follows:

Page 1, line 38, the Word deprivaties should read derivatives, and same page,

line 41, the word derivaties should read derivatives, and page 2, line 37, the

word phenynaphthimidazol should read phmzyZnapM/aimidazol; and that the said Letters Patent should be read with these corrections therein that the same may conform to the record of the case in the Patent Ofiice.

Signed and sealed this 2nd day of November, A. D., 1909.

C. (J. BILLINGS,

Acting Commissioner of Patents.

thylamin, alpha-naphthylamin-6- or 7-sulfonic acid or on using carbonyl-1.2-diamino- 5-naphtl1ol 7 sulfonic acid, meta aminophenyl 1.2 naphthothiazol-5-oxy-7-sulfonic acid, etc. as end components.

We claim:

1. The herein described new azo dyestufi's obtainable from aminoazo compounds which contain in the first component which is a benzene derivative a negative group in ortho-position to the amino-group with the hereiubefore defined 2 amino 5 naphthol compounds, which dyestufi's are, after being dried and pulverized, in the shape of their alkaline salts dark powders soluble in Water, soluble in concentrated sulfuric acid with from a violet to green color; yieldin upon reduction with stannous chlorid an hydrochloric acid an ortho-substit-uted amin of the benzene series, a diamin and a derivative of a 2.6-diamino-5-naphthol compound of the above given formula; and dyein cotton from red to blue shades, substantia 1y as described.

[SEAL-1 Corrections in Letters Patent No. 933,446.

2. The herein described new azo dyestuif which can be obtained from anilin-ortho-sul' fonic acid, cresidin and 5-oxy-L2-phenyluaphthimidaZ0l-7-sulf0nic acid, which dyestufi' is, after being dried and pulverized, in the shape of its sodium salt a dark powder which is soluble in water with a reddishviolet color and which is soluble in concentrated sulfuric acid with a blue color; yielding upon reduction with stannous chlorid and hydrochloric acid anilin-ortho-sulfonic acid, 2.5-dia1nino-4-1nethoxytoluene and 5- oxy-1.2-phenynaphthimidazol-G-amino-T-sulfonic acid; and dyeing cotton blue shades, substantially as described.

In testimony whereof We have hereunto set our hands in the presence of two subscribing witnesses.

Witnesses O'r'ro KoNIG, C. J. WRIGHT.

It is hereby certified that in Letters Patent No. 933,4:46, granted September 7 1909, upon the application of Leopold Hesse and Oscar Gunther, of Elberfeld, and

Arthur Zart, of Vohwi'nkel, near Elberfeld, Germany, for an improvement in Azo Dyes, errors appear in the printed specification requiring correction as follows:

Page 1, line 38, the Word deprivaties should read derivatives, and same page,

line 41, the word derivaties should read derivatives, and page 2, line 37, the

word phenynaphthimidazol should read phmzyZnapM/aimidazol; and that the said Letters Patent should be read with these corrections therein that the same may conform to the record of the case in the Patent Ofiice.

Signed and sealed this 2nd day of November, A. D., 1909.

C. (J. BILLINGS,

Acting Commissioner of Patents.

It is hereby certified that in Letters Patent No. Hiy -H6, granted September 7,

1909, upon the application of Leopold Hesse and Oscar (li'inther, of Elherfeld, and

Arthur Zart, of Vohwihkel, near Elherfeld, Germany, for an improvement in A20 Dyee, errors appear in the printed speeitiration requiring correction as follows:

Page 1, line 38, the word deprivatiee should read dur/il-afimw, and same page,

line ii, the word derivaties should read (w'vu/fvim, and page 2, line 37, the

word phenynaphthimidaze] Should read p/imrq/m/p/iMiniMme-0f; and that the said Letters Patent should be read with these corrections therein that the same may conform to the record of the ease in the Patent Office.

Signed and sealed this 2nd day of November, A. 1)., 1905).

[SEAL] C. (I. BILLINGS,

Aczfiag (,hin'nu'esionm' of Patents. 

